N-bromobutanimide → 5-Bromo-3-fluoro-2-hydroxy-4-methoxybenzoic acid

HRID 629479Notes

Reaction equation

HRID 629479 reaction equation
[F:1][C:2]1[C:3]([OH:13])=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].C1C(=O)N([Br:21])C(=O)C1>CN(C=O)C>[Br:21][C:9]1[C:10]([O:11][CH3:12])=[C:2]([F:1])[C:3]([OH:13])=[C:4]([CH:8]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 847699353-Fluoro-2-hydroxy-4-methoxybenzoic acid

Product 1

HCID 848075045-Bromo-3-fluoro-2-hydroxy-4-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-fluoro-2-hydroxy-4-methoxybenzoic acid (7.30 g) in DMF (70.0 mL) was added NBS, and the mixture was stirred at 25° C. for 2 hr. The solvent was evaporated under reduced pressure, and the residue was diluted with ethyl acetate. The mixture was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (8.86 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washThe mixture was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5d0f347f800e4cba9730170a4ddecd97
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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